Triethylamine → HCID 484993, compound

HRID 1861801Notes

Reaction equation

HRID 1861801 reaction equation
Cl.[Br:2][C:3]1C=C[C:6]([CH2:7]N)=[CH:5][CH:4]=1.C([N:13]([CH2:16][CH3:17])CC)C.[N:18]1[C:27]2[C:22](=[CH:23][N:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[C:28]([OH:30])=O.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CCOC(C)=O>[Br:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:17]=1[CH2:16][NH:13][C:28]([C:19]1[CH:20]=[CH:21][C:22]2[C:27](=[CH:26][CH:25]=[N:24][CH:23]=2)[N:18]=1)=[O:30]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27240964-Bromobenzylamine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 484993HCID 484993, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirring solution of 4-bromobenzylamine hydrochloride (97.8 mg, 98%, 0.431 mmol) in anhydrous DMF (5 ml) was added triethylamine (60.1 ul. 0.431 mmol), After 5 min, 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol), 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol) and 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (60.6 mg, 0.316 mmol) was sequentially added. The resulting mixture was allowed to stir at room temperature for overnight and it was found to be clear. The solvent was removed under vacuum and the resulting residue was redissolved in CH2Cl2 (100 ml). The resulting mixture was allowed to stir at room temperature overnight and it was found to be clear. The solvent was removed under vacuum and the resulting residue was redissolved in CH2Cl2 (100 ml). The organic layer was washed with aqueous NaHCO3, dried over anhydrous MgSO4, and concentrated to give the crude mixture. Chromatography of the crude (Hex:EtOAc=1:1 to pure EtOAc) afforded desired product as white solid (97 mg, 99%): m.p. 149-150° C.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe resulting residue was redissolved in CH2Cl2 (100 ml)
  3. stirringto stir at room temperature overnight
  4. customThe solvent was removed under vacuum
  5. dissolutionthe resulting residue was redissolved in CH2Cl2 (100 ml)
  6. washThe organic layer was washed with aqueous NaHCO3
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customto give the crude mixture

Sources & evidence

ORD record
ord-a05636699e1b4cdbae696f03e085efce
Source dataset
uspto-grants-2003_03
Patent number
US06534520B2

Reaction notes

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